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Details

Stereochemistry ABSOLUTE
Molecular Formula C41H63NO15.C2H4O2
Molecular Weight 869.9886
Optical Activity UNSPECIFIED
Defined Stereocenters 20 / 20
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROTOVERATRINE B ACETATE

SMILES

CC(O)=O.CC[C@@H](C)C(=O)O[C@H]1[C@H](O)[C@H]2[C@@H](CN3C[C@@H](C)CC[C@H]3[C@@]2(C)O)[C@@H]4C[C@@]56O[C@@]7(O)[C@@H]([C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]5[C@]14O)[C@]6(C)CC[C@@H]7OC(=O)[C@](C)(O)[C@@H](C)O

InChI

InChIKey=ONLYWKYYAQXZKP-OKVAQDKSSA-N
InChI=1S/C41H63NO15.C2H4O2/c1-10-19(3)34(47)56-33-28(46)27-23(17-42-16-18(2)11-12-25(42)38(27,9)50)24-15-39-32(40(24,33)51)30(54-22(6)45)29(53-21(5)44)31-36(39,7)14-13-26(41(31,52)57-39)55-35(48)37(8,49)20(4)43;1-2(3)4/h18-20,23-33,43,46,49-52H,10-17H2,1-9H3;1H3,(H,3,4)/t18-,19+,20+,23-,24-,25-,26-,27+,28+,29-,30+,31-,32+,33-,36-,37+,38+,39+,40-,41-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C2H4O2
Molecular Weight 60.052
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C41H63NO15
Molecular Weight 809.9366
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 20 / 20
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Protoveratrine B is one of two alkaloids isolated from the plant Veratrum albumen. The main effect of both alkaloids is vasodilation in all vascular beds thereby reducing blood pressure. In the 1950's it was recognized that Protoveratrine B is the preferred compound which can be administered at significantly higher doses before the patient begins to vomit.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
402 pg/mL
0.5 mg single, oral
PROTOVERATRINE B plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
Protoveratrine B was administered to hypertensive patients as an oral tablet. Doses began at 0.3 to 0.5 mg single daily dose and raised incrementally until a marked fall in blood pressure was observed or the development on vomiting prohibited further increase.
Route of Administration: Oral
In Vitro Use Guide
Brain cortex slices of adult guinea pig were incubated for 30 min with 0.1 mM L-dopa. Brain slices were then pretreated with 5 uM protoveratrine (10 uM to 10 mM) for 20 min at 27 deg-C. Slices then incubated with glucose and L-dopa at 37 deg-C. The inclusion of Protoveratrine caused a decrease in the accumulation of L-dopa compared to control.
Substance Class Chemical
Record UNII
X8GH0703YA
Record Status Validated (UNII)
Record Version